2 days in Tuscany

You're asking lots of the right questions. Please read up on the area, and come back with your remaining questions.
This guidebook also covers Tuscany. https://store.ricksteves.com/shop/p/florence-guidebook

As well, did you book your accommodation for 2 nights or 3? You need 3 nights for have 2 FULL days for the region. Where, more exactly did you book your hotel, where are you coming from, and where are you going after you leave the area?

Sharing your full itinerary might be useful so the folks here can see the bigger picture.

Yes, a guidebook is going to be extremely helpful for planning your trip and answering some of your questions. The community here is happy to help but your questions are a bit too broad to be tackled. For instance, we've no idea what your family is even interested in doing/seeing on your trip. One person's 'must do' isn't necessarily another's. How much time will it take to see ___ (city)? LOL, how long is a piece of string?! A dawdler like me can spend days poking interesting corners that others may rush though in a couple of hours.

As others have said more details would be helpful: Where are you booked and what are your interests?

With a family in tow I would expect you have a set window for how much/long you are going to be "doing stuff" each day.
I would probably recommend choosing 2, 3 - or at most 4 - towns or attractions and spend some quality time at them and really explore. Whether that's a farm, windery, small town, whatever it is choose what you can enjoy and just do those things.
Trying to do too much all the time is a recipe for tired, cranky family and little enjoyment.

While Tuscany is dotted with amazing and different hill towns and farms and wineries a big part of the attraction is the slower pace of life more in touch with the land and the seasons and the people around you. If you want the real Tuscany experience leave room to breathe and just soak it in. It is as beautiful as everyone says but you need time to look at it and appreciate it.

And park in the edge of town parking lots.

Please feel free to ask follow up questions but this is my general response.

My $.02,
=Tod

We found Siena to be a little difficult to find parking in. Many people visit by bus from Florence as they're dropped into the center of the city. It's a 1/2 day destination.

San Gimignano is maybe a 2 hour destination. Parking is on the outskirts of the city, and it's best seen very early or late in the afternoon whenever the tour buses are not in town.

We really enjoy Volterra which is a larger hilltown to the west. It's a half day destination too. Parking is on the edge of the city--as you come up the hill--in a parking garage. Don't worry about a ZTL as they're pretty easily spotted. And don't worry about safety outside big cities.

You might want to go to the bookstore or library and get some travel guides on Italy and/or Tuscany.

In Siena, we always park up the hill by the stadium.

Thank you all for the replies.
My itinerary is as follows.
4 Nights in Rome, then 2 nights at Praiano (Amalfi Coast)
from Amalfi Coast to Montepulciano (Via Naples, where I will rent the car from and will return at Venice Later)
Stay 3 nights at Montepulciano in a Wine Resort (Agritourismo)
4'th day early morning off to Florence. 2 Nights at Florence
After than 2 nights at Venice and then to Montreux (Swiss)
This is my first trip to Europe and will be travelling from Toronto.

We have a mix of interests. Not sure if my Kids will like too much of history. But they love art.
We like beautiful landscapes, the reason why we chose val d'orcia for our stay. As Tod pointed out, we would like to move very casual, not rushing much even if we cannot include all sights. But wanted to make sure right things getting onto our priority lists.
Any tips on driving around Tuscany (may be any links ?) will be appreciated.

Thank you all.
Bijoy

How will you travel from Rome to Praiano? Then to Naples?

I’d add a night to Praiano
It’s going to take better part of the day to get there
A 2 night stay is really just 1.5 days in location

You might want to drop the car BEFORE Florence as you really don’t want or need the car there
Chiusi would work as a drop off location then train to Florence ( could also work as pick up
Avoid that long drive/pick up in Naples)

I'd also add a night to Montepulciano resort- that's a long trip from Naples to Montepulciano- Day 1 is gone by the time you get there, leaving you just 2 full days. SG, Volterra, Siena are all at least 1.5 hours away and each deserves a solid half day at minimum.
SG, Voltera, Siena all lovely but not really IN Val D'Orcia.
Places closer to visit- Pienza, Montalcino , Monticchielo, Bagno Vignoni, San Quirico.

Basically all Tuscany hill towns are ZTLs- you will not be driving INTO any of these towns, park outside the walls.

Train to Venice from Florence

Bijoy, it sounds like you and your family are interested in walled cities. Many towns of various sizes in Tuscany once were walled in, and may now have bits and pieces of ancient walls, basically ruins. One small town which is still fully surrounded by its ancient wall is Monteriggioni, which is very near Siena, on the road to San Gimignano actually. You might make a stop of an hour or two there, I think you can walk all the way around the top of the wall. I have not been there, but it has been on my to-do list. Another town with a wall all around it is Lucca, but that is much further away from where you plan to be. Lucca is fun because the wall is very wide with lawns and a path on top. Many people picnic or ride bikes on top of the wall, especially fun for kids.
Sounds like you are planning a wonderful visit to Italy for your family!

• What are the must-see places?
• How much time I would need at all these places?
• Are all cities walled? -Is there a ZTL region in all cities?

You have a good list of places. We spent a week in Tuscany staying at an agriturismo and visited Siena, San Gimignano and Volterra.

For time, as someone said, doing San Gimignano and Volterra in a day is feasible. We spent the morning in San Gimignano, grabbed a beer and slice of pizza from a little cafe and headed to Volterra. We planned to head back to our home base earlier, but we stumbled onto the passeggiata, or evening stroll just outside the walls of Volterra. It was fun seeing the citizens visiting and the sunset was spectacular, well worth the stay. We devoted an entire day to Siena, which I consider a minimum amount of time.

Not all towns and cities are walled. We stayed just outside Greve, which is not walled. I'd say all walled cities are ZTL inside the walls. That's a good rule of thumb to go by. There should be enough parking, but you are going in the height of the season. I think safety concerns are a little exaggerated, just follow some basic guidelines, such as make sure nothing left in the car is visible and park in public areas. We never had a problem and I felt my car was safer there than in many parts of Atlanta.

There is underground parking in Volterra. There is also parking at the other end of the town. There's a large lot just outside the main gate at San Gimignano. We parked at the stadium in Siena, but it may fill up early in June.

Thank you Doug, Larry , Christine and everyone for all your tips.
Refining my itinerary based on inputs which I could accommodate keeping by schedule intact.
I will cut one stay in Montepuliciano and move to north (San Gimginano) for 1 stay. That way Florence is nearer for me on Day4 morning.
Christine, I liked the idea of renting car from Chiusi (Avis, we have some corporate discount too :))
Will take a train from Napoli to Chiusi and rent the car.

BTW how is the traffic from San Gimignano to Florence train station ? Is driving in Italy easy ? I see net flooded with Italian driving experiences, which made me to choose alternatives in Amalfi Coast.

My target parking stations will be as below (Posting this as someone van benefit in future :))
Siena Parking / Parking Il Campo, Via Sant'Agata, 53100 Siena SI, Italy
Volterra Parking / Parcheggio La Dogana Srl, Piazza Martiri della Libertà, 56048 Volterra PI, Italy
San Gimignano Parking / Parcheggio 2 Montemaggio, Piazzale Martiri di Montemaggio, 53037 San Gimignano SI, Italy

From Roma termini take the train to Napoli centrale. (1hr 17 m) From Naples either take the Circumvesuvian to Sorrento (1H 30m)then a bus to Praiano (1H15m)
Total of time to do this, all three modes of transportation is (4 hours) Your best bet is to hire a private driver from Napoli central directly to Praiano. Cost will be about €120.

To travel by train from Naples to Chiusi, again take a Private driver. This train will save you some time. There are no changes.

Intercity 590
SEE SERVICES
10:31
Napoli Centrale
Fermata: Napoli Centrale

Partenza: 10:31

10:47
10:49
Aversa
Fermata: Aversa

Arrivo: 10:47

Partenza: 10:49

11:20
11:22
Formia-Gaeta
Fermata: Formia-Gaeta

Arrivo: 11:20

Partenza: 11:22

11:58
12:00
Latina
Fermata: Latina

Arrivo: 11:58

Partenza: 12:00

12:37
12:40
Roma Tiburtina
Fermata: Roma Tiburtina

Arrivo: 12:37

Partenza: 12:40

13:12
13:14
Orte
Fermata: Orte

Arrivo: 13:12

Partenza: 13:14

13:43
13:45
Orvieto
Fermata: Orvieto

Arrivo: 13:43

Partenza: 13:45

14:08
Chiusi-Chianciano Terme

For driving in Italy, download this e-book. Yellow banner on bottom of page.

https://italybeyondtheobvious.com/

Parking in Siena, use either the Stadio lot or the one by the train station. Use the escalator to the top for the station.

Drop your car in Siena after visiting Volterra and San Gimignano and take the bus to Florence. 1H17m. Then train to Venice. 2H 15m.

For trains use https://www.trenitalia.com/en.html

Amalfi coast bus timetable.
https://www.sorrentoinsider.com/en/sorrento-to-positano-bus-schedule

This blog should give you an idea of getting around in Praiano. It’s one of the prettiest towns on the coast but please take note of the stairs with the twins.

https://iowagirleats.com/life-on-the-mediterranean-coast/

Thank you, Gerri. That was so much of details. Appreciate that.
1 more question. Is Conque Terre similar to Amalfi? Shall I be visiting this place by squeezing my schedules?
Can I do Pisa and Cinque Terre in 1 day from Florence?

Thank you in advance
Bijoy

Shall I be visiting this place by squeezing my schedules? Can I do
Pisa and Cinque Terre in 1 day from Florence?

No. If you only have two nights/1.5 days for Florence, you need all of that time just for Florence. I'd go a little easy on how much moving around your family has to do?